And few things grate at Mr. Trump like the prospect of disloyalty. Close allies have turned on him in the past, including his former personal lawyer and fixer, Michael D. Cohen, whom Mr. Trump has labeled a “rat.”
Mr. Cohen, who pleaded guilty to federal charges related to hush money payments to two women who said they had romantic affairs with Mr. Trump, is cooperating with the Manhattan district attorney’s investigation. After pleading guilty, Mr. Cohen said that it was Mr. Weisselberg who had helped the Trump Organization to disguise the reimbursements that Mr. Cohen received for paying off one of the women.
Mr. Weisselberg was not accused of any wrongdoing by federal prosecutors, and Mr. Trump did not pardon him in his final days in office, though he was said to have considered doing so. (A pardon would not have given Mr. Weisselberg immunity from state charges.)
After Mr. Cohen pleaded guilty in 2018, Mr. Trump expressed confidence that Mr. Weisselberg had not turned on him.
“One hundred percent he didn’t,” Mr. Trump told reporters for Bloomberg. “He’s a wonderful guy.”
Mr. Weisselberg is, in certain respects, the polar opposite of his longtime boss. Discreet and unassuming, the financial chief has avoided attention even as he has brought his family into Mr. Trump’s orbit. One of his sons, Barry, was the property manager of Trump Wollman Rink in Central Park. Another, Jack, works at Ladder Capital, one of Mr. Trump’s lenders.
But Mr. Weisselberg has done his part to contribute to Mr. Trump’s aura of wealth and power. In 2005, when The New York Times attempted to determine how much money Mr. Trump had, Mr. Weisselberg provided a list of assets that he said would show that Mr. Trump was worth $6 billion.
When the list of assets appeared to add up to only $5 billion, Mr. Weisselberg excused himself.
“I’m going to go to my office and find that other billion,” he said.